Gender: Confused
by HiddenHikariAppend
Summary: When Dean reveals something very personal to Sam at a young age, it causes Sam to think about himself deeper than he had before. When you get a certain angel who's already not too accustomed to human ideas on gender involved, as well as some other touchy subjects, it becomes increasingly complicated, as well as dangerous. (Warnings within!)
1. Chapter 1

A/N: Before I begin, I'll go ahead and warn you this fic deals with gender a great deal. Misgendering as well as slurs may occur from certain characters, as well as within the beginning of the narrative in order to explain the situation as it grows. I have no definitive plans for what will happen in later chapters, only that there will be quite of few of them. Do not be alarmed if I add "major character death" onto the archive warnings. Lastly, I am *not* cis gendered, although I'm not trans either. If the narrative includes anything mistakenly transphobic, please inform me. Please do not tell me these issues in the comments and PM me about them instead, I would much rather talk about these things privately if at all possible. I do not need to be informed of anything hurtful said by a character, because it was said that way on purpose - only things mistakenly said in the narrative, please! You've been warned now that this fic will include subject matter that might make you uncomfortable and/or triggered and I encourage you now to leave the fic if it is not something you will be able to handle. Thank you for reading thus far and thank you if you continue on to the fic itself!

Tiny, light footsteps padded through the hotel suite, from one bedroom to another, before a small knock rapped against the door. Sam opened it to find his older sister, several inches taller than him, but the rest of her still the size of an 11 year old girl. He smiled up at her, "Deanna?"

Deanna pushed past him into the room serving as his while their dad was out hunting, she plopped down on his bed and grabbed at a book he had left open there. She thumbed through it a bit before loosing his place and dropping it back onto the bed. Sam followed her into his room, sitting beside her on the bed. He watched her eyes dart from him to the floor to an empty spot on the wall. She was distracted, or nervous? He couldn't tell.

Deanna took a deep breath before speaking, "Listen Sammy, I know you're still really young, but I think you're smart enough to understand what I'm about to say, okay? And I don't want you to laugh, I want you to take me seriously, okay? Can you do that?"

Sam nodded his head, "Sure, sis! What is it?"

Deanna grimaced a bit, "Another thing, don't tell dad."

Sam nodded again, eager to hear the big secret she had to tell him. She watched his eyes, curious and excited. Her's we're almost the complete opposite. She decided to stand when she told him, then realized sitting might be better. Sam watched as she stood, paced, sat and thought, stood again for barely a second before sitting again. The smile slowly faded from his lips and the curiosity dulled in his eyes. It was all replaced with worry.

"Deanna...you can tell me anything." He spoke solemnly, "And I promise not to tell dad, or laugh, or anything...are you okay?"

Deanna smiled a bit at this. He really was smart for his age. At the young age of seven, Sam heard his sister correct something about herself, out loud, for the first time in his life. He listened as she told him she was not his sister, but in fact his brother. He watched the small tears well in his older brother's eyes before he quickly pushed them back. He listened to him explain that this had been his feelings for a very, very long time. He spoke of how lucky he was that their father had never questioned his wardrobe or hair style. He heard his voice waver for only a second before he demanded Sam to never refer to him as Deanna again.

Sam smiled up at him, "Then what do I call you?"

He thought for a moment, as if this was the first time that issue had come up, "Dean. Call me Dean."

Sam smiled again, "Okay, Dean!"

Dean's eyes welled again, and this time he didn't hold anything back as he leaned forward and took his baby brother in his arms. Sam hugged his older brother back before pulling away and tilting his head to one side. "I don't understand one thing though...why are you so worried about dad knowing? What does it matter if you're my big sister or my big brother?"

Dean half smiled as he searched the innocence in his brother's eyes, "I hope you never have to understand, Sammy. I hope you never have to feel like this."

Sam still didn't quite get it, but his nodded his head and smiled once again up at his older brother.

Goddamnit were they annoying.

Sam felt the doorknob leave the palm of his hand and heard the screen door snap back into place, clattering around loudly. He yanked his hood over his head and shoved his hands deep into his jacket pockets. For a moment he thought about grabbing the keys to the Impala and just driving off. It wouldn't be the first time. But then, he thought, he'd have to venture back into the bunker and see those too sucking face.

Did he mention how annoying they were?

Yes, he did, numerous times throughout the day – increasingly more often as the sun set.

Well, sure, he knew they had years worth of sexual tension built up, and yeah, he was glad to see his brother happy and all but…Jesus Christ was it really that necessary to be all over each other all the time?

Sometimes he thought it would be better if Dean went back to trying to bang a different chick every week, hell he could switch everyday if it meant Sam didn't have to wake up to a certain angel's groaning screams nearly every night. And then that guy thought he could just waltz around in Dean's boxers and make them shitty breakfast as if it were an apology for Sam's lost hours of sleep.

Hell, at least Castiel tried to apologize. The closest Dean came to any sort of 'I'm sorry' were the Burger King coupons he left magnetized to the fridge for him before him and his boyfriend went off to do who knows what at some ungodly time of the morning.

They were seriously so fucking annoying.

Sam dropped onto the couch, flicking on the television. He didn't pay attention to anything that passed across the screen as he flipped from channel to channel, stuck inside his own head. On the upside, being with Castiel meant significantly less days of coming home to holes kicked in walls and upwards of 3 empty ice cream containers surrounding an equal amounts pissed off as much as broken inside older brother.

It was always because of his vagina, and it always made Sam want to track them down and give them a stern educational lesson before punching them square in the jaw. Dean could never quite find anyone to understand. He tried gay guys, but they'd toss the 'tranny' word out the moment Dean's pants fell. The girls were rarely a whole lot different and he was usually just considered 'the best of both worlds,' which helped to piss him off even worse.

Dean tried to put on a tough face, he'd flip em off, gather his clothes (he was known to give a strong ass kicking to the particularly giggly ones), and storm back home to usually yell at Sam about something totally unrelated.

Sam didn't take it to heart. He'd apologize for whatever wasn't his fault, maybe buy a six pack, on particularly bad days he'd HBO some porn and leave for a couple hours. It had almost become routine before Cas asked the question that had been sitting on both Sam and Dean's minds for a good twenty plus years now: "I don't understand why you humans believe God created over seven billion of you, your personalities as unique as your DNA, and yet...a single body part decides one of two categories."

Sam and Dean had looked at each other.

Given out of context, it might seem a little out of the blue, but when you factor in that Cas had been admiring a particularly feminine-looking dress shirt, and had been redirected to the opposite side of the store by a sales clerk, only moments before, it made quite a bit of sense why he was confused about this. "It's only genitalia...it's not a like or dislike...why does it go so far as to tell me which side of the store I am allowed to shop in?"

They were seated outside of a small dinner, Dean's mouth full, Sam sipping a drink, and Cas's food completely untouched; the issue on hand distracting him. Sam leaned forward around his drink, "Well, I don't really know why people think that, I think it's just because that's the way it's always been. There are boys and girls, and they just act differently, Cas, is it really that big of a deal?"

Dean held up his drink and smirked almost like what Sam said deserved a toast, "Boys and girls are on totally different spectrum, Cas." He smiled as he leaned forward, grabbing at a fry off Cas' plate.

Cas still looked a bit dumbstruck, "No. That is not right at all. I have watched humans for centuries, I've seen how you have developed, I've watched these...genders slowly become more and more prominent. I understand how they've come into existence: stupidity. What I do not understand is why they continue to be so prevalent."

Sam leaned back and looked at Dean, Dean gave him one of his 'don't ask me I have no Earthly idea what he is even talking about' kind of looks. "Well, I don't really know, Cas."

"I may not be a human, but I know I am neither of those things. I am not a woman nor a man. I am not going to play along with this silly game. This body is not even mine, why should its sex determine my gender?" Sam and Dean shared another look of 'what exactly is going on.' "Women and men may look however they please and own whatever body parts they happen to have, and you are also allowed to be neither. I may not be human, but I know this silliness is not what my father had in mind when he made it possible for you to recreate." Cas stood up, picking up his drink, "After all, recreation and pleasure are the only reasons you even have them, not to determine your worth or who you are." With that, Castiel turned away, walking down the sidewalk.

Sam watched his back for a moment before locking eyes with his brother, "Should we g-"

Dean started laughing. He doubled over, having to set his burger back down on his plate to keep from dropping it. He finally sat up and wiped at a tear in his eye, "Did you hear that guy? Did he really just preach to _me_ about how I don't need a penis to be a man?"

"I really don't think that was his main point. And he doesn't know about you, Dean."

"No, I know, I know - I'm not mad. I just think it's funny, he really thought we we're gonna judge him, ya know? I mean, here I am with a tampon in and you've got hair like some kinda hippy, and he's telling _us _about gender roles?" Dean started laughing again.

Sam made an uncomfortable face. "I'm gonna go catch up with him."

Dean stood up first, pushing his empty plate towards Sam. "Wait, I'll go talk to him. You throw this away, okay?" Sam rolled his eyes and took the plates as Dean jogged off down the sidewalk in search of Castiel.

Any other day, Cas probably would've just poofed off somewhere else, but today he had a lot on his mind, and walking seemed to help. He only had about five minutes to himself before he heard someone's heavy breathing behind him before he turned to see Dean slow down his pace as he caught up with him. "Hey, man, where ya going?"

"Nowhere."

"Doesn't seem like nowhere, seeing as how we're definitely walking towards that liquor store."

"I'm not buying liquor."

"Are you buying _me_ liquor?"

"I'm not buying liquor, period. I'm just walking. That's all."

Dean nodded a little in understanding as Cas took a glance from side to side before the two crossed a street. Dean had his hands shoved into his pockets, Cas's dangled by his side, brushing against the hem of Dean's jacket occasionally. "Listen Cas, back there, we weren't trying to argue with you or anything, okay?" Cas was silent. Dean wasn't sure if he was waiting for him to continue or ignoring him. "I mean, I totally get where you're coming from. I really do. Gender is stupid, and if you don't want to be part of it, then don't be. That's cool. I'm actually pretty sure more people than we realize are like that." Cas gave Dean a sidelong glance and Dean realized he finally caught his attention. He smiled as he spoke next, "I mean, its the 21st century, Cas! Women grow their leg hair, men have vaginas, people are breaking it. It's difficult and we get a lot of shit for it and its dangerous sometimes, but its-"

"We?"

"Did I say 'we'?"

"Yes, Dean."

Dean fell silent for a moment. Cas didn't break it.

"Look, all I'm saying is that we're on the same page here. You ain't got a gender? No big deal. All I care is if we can loop back around this block and hit up that gas station and grab a couple six packs." Dean smiled. Cas' lips slowly tugged up to barely hint at a smile as well.

"Thank you, Dean."

"Don't mention it."

Fast forward a couple weeks, and Dean and Cas had found that by sharing these ideals in common, it made them a perfect match, as if it hadn't been obvious to Sam for months beforehand. So we find Sam back on the couch, flicking through the channels again, thinking back to that day. There was one little sentence that pricked at Sam, refusing to let him settle with exactly what had happened that day.

Why in the hell did Dean always _need_ to mention his hair?

Almost instinctively, he reached up and touched it, combing his fingers through it. Okay, so maybe it was sort of long for a guy. Yeah, that one waitress saw him from behind and called him a girl that one time, but there was something about the teasing in Dean's voice whenever he mentioned it, something that put him off, made him crinkle his nose like he smelled something bad.

Dean made so many assumptions about him. He thought about telling him, but he didn't even know the right words to use to explain himself. He reached towards his laptop, flicking it open and staring at the google homepage for a solid minute and a half, just trying to figure out what to search for. He barely typed out two letters before he heard the bunker door swing open, Dean and Cas stumbling back in, trying to be as quiet as they could, but Sam could hear their lips locked together. He rolled his eyes as they thudded their way into Dean's room. He closed the laptop, rubbing at his eyes, his face in his hands. He sat like that, listening to their noises waft from the room before standing up and snatching the keys off the counter and whisking out the bunker into the night, alone.

A/N: Shout out to tumblr user carry-on-my-wayward-butt who's rad headcanon slam with me and a couple other anons inspired this fic like literal months ago before it got lost in my drafts!


	2. Chapter 2

Sam revved the engine to the impala, he sat for a moment, waiting for Dean to burst out of the bunker and ask him just where in the hell he was going in his car. Dean didn't appear. Figures, Sam thought. As if Dean's head wasn't so far up Cas' asshole he could ever notice Sam had left. He pulled out onto the road, his foot lead as he sped down the highway. He could hear his own voice echo in his head yelling at Dean to slow down. He hadn't done that in weeks, he and Dean rarely ever drove together anymore.

He wanted it to piss him off, he wanted to talk to himself rationally about how he shouldn't be angry over it, he wanted to slowly realize that Dean was in love and he should be happy after he finally found someone to love him for himself. He wanted all of that, but in order for that to happen, he'd have to be angry in the first place. To be completely honest, he wasn't angry, he was almost entirely the opposite.

He wanted to cry. He wanted to barge into Dean's room, tell him he was there for him when he still went by 'she.' He wanted to throw a tantrum and act like the child he never got to be. He also kinda wanted to punch Cas and tell him it would be totally cool to just leave Dean alone for like ten minutes sometime. He wanted to do and say a lot but he didn't, he just gripped the steering wheel tighter, watching the speedometer increase still, the trees on the side of the highway a blur in the corner of his eye.

He slowed down somewhat as the lights of town came into view and he found himself crawling down the main strip, chewing at the inside of his mouth as he glanced at all the open bars, drunkards wobling their way from one to another. That was he and Dean a few weeks prior. Well, it was Dean anyway. He'd get wasted and hit on people while Sam sat nearby and watched him. At some point in the night, Sam would step in, excuse Dean for whatever unwanted drunken compliments he had given, and help him back out to the car.

Sam would drive them around while Dean thrashed around in the passenger seat, mumbling some nonsense about 'just wantin' to get laid' and 'why it was always such a big deal.' Sam would tell him it didn't matter to him, that he never cared. That's what he always said. Dean would thank him, but by the morning he didn't remember a single sweet thing to fall from Sam's lips. Sam knew he wouldn't, that was the only way he could bring himself to say that kind of stuff. His mouth-chewing increased as he thought about how Cas could say whatever he wanted to Dean, day time, night time, drunk or sober, it didn't matter. That was what pissed him off.

Sam slammed on his breaks as he almost ran a red light, too caught up in his own head. He scolded himself before waiting for the light to change and finding a nice to curb to park by. He locked the car as he got out, his hands shoved deep in his pockets, one fingering at the keys, the other gripped tight into a fist. He waited for a couple cars to pass before jogging across the street. Downtown got pretty busy at this time of night, music spilling out of nearly every bar, attracting people from all sides of town.

Dean only had a select few bars he ever went to, never one to venture to far out of his comfort zone. He knew which ones had the cheapest whiskey and the hottest girls and that's where he stayed. Sam, always being the designated driver of the two, stayed sober and drank water or soda on the house, trying not to stray too far from his soon-drunken brother. Without Dean here, he was finally able to explore, glancing through the windows of several bars they usually glossed over on their nights out on the town.

After a few minutes of seeing what looked like the same bar set up over and over, Sam stumbled across one with a very different atmosphere. He didn't try to sugar coat it for himself, it was a gay bar. The neon sign in the window didn't even attempt to tone it down, either. With nothing more than a quick glance over his shoulder, he pushed the door open, shuffling into the crowded room.

Crowded was an understatement. Men ground against one another on every side of him and women ran their hands up the thighs of other women. Voices dropped to a whisper as he walked by. He felt a hand slide from one shoulder blade, across his back and coming to rest on his hip as a man suddenly appeared, attached the arm that rested against him. "Hey, aren't you Dean's brother?" he cooed and Sam gave a nervous nod. "Where is she?" he asked and Sam took a double take.

"Excuse me?" He asked a bit louder, trying to be heard over the music.

"Dean? Your sister?" The man glanced around, searching for the shorter man, "She not with you?"

"I-I'm sorry, 'sister?'" Sam's hand reached down and picked the man's fingers off his side, staring down at him.

The man scoffed, "Oh, my bad, brother," he gave a dry laugh, "well, you tell him I say for him to get his ass back down here soon, alright?" He turned around, tossing a wave over his shoulder as he disappeared back into the crowd.

Sam's blood was boiling. He pushed through the crowd further, making his way to the bar. He pulled out a stool, taking a seat and folding his hands in front of him. He waited patiently for a bartender to notice him. It was a women, not much older than himself. She took a long look at him, leaning over the counter, a hand reaching out to twirl his hair around her finger, "Hey sug's" she drawled, "what is you?"

Sam's eyebrows furrowed, and for the second time that night, he found the phrase 'excuse me' falling out of his mouth, soaked in confusion with a hint of distaste. For a moment he thought maybe she was another hunter, and was trying to ask him if he was as well. Maybe she had a case or - "I mean, what you got in your pants?"

Sam sat up, tugging his head away from her, pulling his hair to fall back against his cheek, one hand instinctively reaching to tuck it behind his ear. "I, ma'am, I'm not really sure what you're-"

She scoffed, "Kid it ain't no big deal," she gave him a wink, "I just like to know what I'm gettin' my hands on."

Sam scrunched up his nose. What is you? kept repeating in his head over and over as he shook his head at the lady, "I, look I'm not interested in...I just want a drink, please."

She rolled her eyes and turned her back on him, "Fine, but if you're gonna be hangin' round here long, you better get used to those kinds of questions, kid." She fixed him a drink and slid it towards him. "A lot of 'em out there, they don't take kindly to people like yourself."

Sam knitted his eyebrows together, "...straight people?"

She all but laughed in his face, "Son? You think you're straight?" She whipped at her eyes, "Even if you were, that ain't what I'm talking about. I mean you uh, what do you call yourselves? Non-bi-somethings?" She shrugged as she glanced at someone who took a seat a few stools down from Sam, nodding in their direction and informing them she'd be with them soon.

"Hey, lady, I think you're confused, I'm not uh...whatever it is your talking about." Sam swished his drink around a couple times before knocking it back, swallowing hard. "I think my brother and his boyfriend comes here sometimes. Dean? You know him?"

The woman looked up from where she poured a drink a ways down the bar from him, "Dean? Shoo, he's a rough one, that one." She finished the glass, sliding it to the patron before walking back over to stand across from Sam again. "Why, is everything okay? He ain't hurt is he?"

Sam shook his head, a small smile playing on his lips, "No, no everything's fine...I'm just...I don't know. Him and Cas, they've been doing their own thing for a while and I guess I just wanted to see what all the fuss is about." He watched as she held a bottle up and he nodded at her as she refilled his glass. He didn't give the bubbles time to settle before tossing his head back, his hair bouncing back from where it was previously tucked behind his ear.

She giggled as it did so, "Damn boy, with hair like that...you ever think of being a drag queen? We ain't go too many good ones in here, I'm sure they'd love you!"

Sam laughed, clearing his throat and shaking his head. "Me? Drag queen? I, uh, no," he laughed again, "I really can't see myself doing that."

She folded her arms, "You sure? It pays pretty well and," she gave him a wink, "it'd give you a pretty great reason to be down here when your brother and his boy are."

Sam peaked at that, his teething finding their way back to chew on the inside of his lips. He was silent for a moment, studying the woman's smirk-clad face before speaking. "How much pay are we talking?"

"Sam? Sam you almost done in there?" a voice called into the small changing room. Sam ignored it, his eyes fixed on the mirror in front of him. More specifically, the figure in the reflection. He knew it was himself, he could see his own bone structure and when he moved, it mirrored him. When he smoothed one hand down his waist to sit it on his hip, the person in the mirror did as well. It was almost unsettling to know it was him, standing there in a knee-length, sequenced dress, painted nails, his hair curled and styled, his face under so many pounds of makeup he was afraid if he touched it, it would peel off in one huge layer. He just kept staring. Someone knocked on the door.

"Yeah, uh, yeah I'll be right out." He tore his gaze away from the mirror, opening the dressing room stall to find a group of five or so drag queens eagerly awaiting him exit. They all gasped and cooed at him, a couple whistling. Sam smiled awkwardly, his hand reaching the back of his neck, "Guys, guys, I-"

The one who had been knocking cocked an eyebrow up at him, "No, no, don't use that kind of language here. We're girls right now."

"I...what?"

One of the younger ones smiled up at Sam, "When we're in costume, we're girls." He gave him a wink, "If you call us guys, it breaks the illusion!"

A third spoke up next, "Speaking of which, what's your name?"

"My name? You gu-girls know my name."

One of them shook his head, "Not that name! Your name now, while your in character!"

Sam was confused, uncomfortable, and every now and then felt he might be sick. This all just felt so wrong. He remembered how complicated it was for his brother when they were younger to get people to call him the right name and having them call him a boy was nearly impossible, and yet these men could just change it so fast as if it were some kind of game. It was sickening.

"Can't Sam be a guy or a girl name? I've known plenty of girl Sam's." He watched a couple of them roll their eyes at his argument.

"How about we meet you half way, Samantha?" one asked and the others gave little nods of agreement, "I think I speak for all of us when I say you're the prettiest girl here tonight!" A few mumbled their agreement and Sam tried to smile.

Prettiest...girl. He felt his hand twist and realized he had it rolled up into an increasingly tight fist. He had relaxed when he heard that, thought. He couldn't explain why, but there was something about it...girl. He forced his smile as the group left from their small pre-show station at the back of the bar and the show began.

-1

Sam stumbled into the backstage area, the others patting him on the back, congratulating him on a great first performance. Sam's smile was no longer forced and it spread from ear to ear. He looked around at each of them, some already pulling their wigs off or pawing at the makeup on their faces. He watched as the girls slowly fell back into their usual, more masculine state. Pants replaced dresses and the lace panties fell to be recovered by boxers.

Sam did nothing. He could hear a couple of them ask him what he was doing, why he wasn't changing, and teasing him about 'enjoying being a girl.' He ignored them as he watched himself in the mirror above the makeup station. His fingers drifted up to the earrings that clipped on and hung from his ears. "Can I keep these?" he asked, somewhat out of the blue, catching one of the others off guard.

"What? Those old things?" He looked around at the others before giving Sam a shrug, "I guess so, I don't think anyone else ever uses them."

Sam gave a slight smile as he unclasped them and found his pile of clothes he had arrived in. He tucked the earrings deep into a pocket and buttoned it closed before ducking back into the changing room. When he was done, he said his good byes to his new coworkers and took his leave from the bar, his fingers idly playing with the earrings inside his pocket.

Sam spent the rest of the night following a trail of Wikipedia articles, jumping from one subject to the next before finally landing on one that caught his eye and finally answered everything he had been looking for: genderfluid.


End file.
